tert-butyl (2R)-2-(3-phenylpropyl)pyrrolidine-1-carboxylate | 847256-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2R)-2-(3-phenylpropyl)pyrrolidine-1-carboxylate
• CAS: 847256-23-9
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: OHQITGZLOQLORY-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-2-(3-phenylpropyl)pyrrolidine-1-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics

  摘要：

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.008
• 作为产物：
  描述：

  (S)-N-Boc-吡咯烷-2-甲醛 N-(叔丁氧羰基)-L-脯氨醛 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (2R)-2-(3-phenylpropyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics

  摘要：

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.008

文献信息

• Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of <i>N</i>-Boc-pyrrolidine
  作者：Christopher J. Cordier、Rylan J. Lundgren、Gregory C. Fu

  DOI：10.1021/ja4054114

  日期：2013.7.31

  Although enantioconvergent alkyl-alkyl couplings of racemic electrophiles have been developed, there have been no reports of the corresponding reactions of racemic nucleophiles. Herein we describe Negishi cross-couplings of racemic α-zincated N-Boc-pyrrolidine with unactivated secondary halides, thus providing a one-pot, catalytic asymmetric method for the synthesis of a range of 2-alkylpyrrolidines

  尽管已经开发了外消旋亲电子试剂的对映异构烷基-烷基偶联，但还没有外消旋亲核试剂的相应反应的报道。在此，我们描述了外消旋 α-锌化 N-Boc-吡咯烷与未活化的仲卤化物的根岸交叉偶联，从而为合成一系列 2-烷基吡咯烷（目标分子的重要家族）提供了一种一锅催化不对称方法。来自 N-Boc-吡咯烷，一种市售前体。初步机制研究表明，两种最直接的对映体聚合机制（有机金属偶联伙伴的动态动力学拆分和简单的 β-氢化物消除/β-迁移插入途径）不太可能起作用。
• Iap binding compounds
  申请人：Shi Yigong

  公开号：US20070032437A1

  公开（公告）日：2007-02-08

  Compounds that bind cellular IAPs (inhibitor of apoptosis proteins) are disclosed. The compounds are mimetics of the N-terminal tetrapeptide of IAP-binding proteins, such as Smac/DIABOLO, IIid. Grim and Reaper, which interact with a specific surface groove of IAP. Also disclosed are methods of using these compounds for therapeutic, diagnostic and assay purposes.

  本文披露了能够结合细胞IAP（凋亡抑制蛋白）的化合物。这些化合物是IAP结合蛋白（如Smac / DIABOLO，IIid Grim和Reaper）N末端四肽的类似物，它们与IAP的特定表面凹槽相互作用。此外，本文还披露了使用这些化合物进行治疗，诊断和检测的方法。
• IAP BINDING COMPOUNDS
  申请人：Shi Yigong

  公开号：US20100261914A1

  公开（公告）日：2010-10-14

  Compounds that bind cellular IAPs (inhibitor of apoptosis proteins) are disclosed. The compounds are mimetics of the N-terminal tetrapeptide of IAP-binding proteins, such as Smac/DIABOLO, Hid, Grim and Reaper, which interact with a specific surface groove of IAP. Also disclosed are methods of using these compounds for therapeutic, diagnostic and assay purposes.

  本发明公开了结合细胞IAP（凋亡抑制蛋白）的化合物。这些化合物是IAP结合蛋白的N-末端四肽的类似物，例如Smac/DIABOLO、Hid、Grim和Reaper，它们与IAP的特定表面凹槽相互作用。还公开了使用这些化合物进行治疗、诊断和测定的方法。
• US7718600B2
  申请人：——

  公开号：US7718600B2

  公开（公告）日：2010-05-18
• Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics
  作者：Haiying Sun、Zaneta Nikolovska-Coleska、Jianyong Chen、Chao-Yie Yang、York Tomita、Hongguang Pan、Yoshiko Yoshioka、Krzysztof Krajewski、Peter P. Roller、Shaomeng Wang

  DOI：10.1016/j.bmcl.2004.11.008

  日期：2005.2

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.